The most stable conformation of the β-pyranose form of each of the given sugars is to be drawn. Concept introduction: A pyranose is a six-membered ring form of a monosaccharide. The Haworth formula is a representation of carbohydrate in a cyclic form where the substituents point up or down on the ring. The Fischer projection is converted to Haworth formula by formation of a six-membered hemiacetal between the aldehyde group and the C-5 hydroxyl group. The substituents present on the right side in Fischer projection will be drawn on the lower face in Haworth formula. The substituents present on the left side of the vertical line in Fischer projection will be drawn on the upper face in a Haworth formula. The substituent (alkyl) at equatorial position in chair form is the most stable conformation.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24.7, Problem 7P

Interpretation Introduction

Interpretation:

The most stable conformation of the β-pyranose form of each of the given sugars is to be drawn.

Concept introduction:

A pyranose is a six-membered ring form of a monosaccharide.

The Haworth formula is a representation of carbohydrate in a cyclic form where the substituents point up or down on the ring.

The Fischer projection is converted to Haworth formula by formation of a six-membered hemiacetal between the aldehyde group and the C-5 hydroxyl group.

The substituents present on the right side in Fischer projection will be drawn on the lower face in Haworth formula. The substituents present on the left side of the vertical line in Fischer projection will be drawn on the upper face in a Haworth formula.

The substituent (alkyl) at equatorial position in chair form is the most stable conformation.

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Draw the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimers

When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react toform an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of d-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of d-glucose exists in the anhydro form under the same conditions.

When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react to form an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of D-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of D-glucose exists in the anhydro form under the same conditions.

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24.7, Problem 7P

Interpretation Introduction

Interpretation:

The most stable conformation of the β-pyranose form of each of the given sugars is to be drawn.

Concept introduction:

A pyranose is a six-membered ring form of a monosaccharide.

The Haworth formula is a representation of carbohydrate in a cyclic form where the substituents point up or down on the ring.

The Fischer projection is converted to Haworth formula by formation of a six-membered hemiacetal between the aldehyde group and the C-5 hydroxyl group.

The substituents present on the right side in Fischer projection will be drawn on the lower face in Haworth formula. The substituents present on the left side of the vertical line in Fischer projection will be drawn on the upper face in a Haworth formula.

The substituent (alkyl) at equatorial position in chair form is the most stable conformation.

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Answer 3

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24.7, Problem 7P

Interpretation Introduction

Interpretation:

The most stable conformation of the β-pyranose form of each of the given sugars is to be drawn.

Concept introduction:

A pyranose is a six-membered ring form of a monosaccharide.

The Haworth formula is a representation of carbohydrate in a cyclic form where the substituents point up or down on the ring.

The Fischer projection is converted to Haworth formula by formation of a six-membered hemiacetal between the aldehyde group and the C-5 hydroxyl group.

The substituents present on the right side in Fischer projection will be drawn on the lower face in Haworth formula. The substituents present on the left side of the vertical line in Fischer projection will be drawn on the upper face in a Haworth formula.

The substituent (alkyl) at equatorial position in chair form is the most stable conformation.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24.7, Problem 7P

Interpretation Introduction